Z-Arg(Pmc)-OH | 112160-32-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: Z-Arg(Pmc)-OH
• 英文别名: (2S)-5-[[amino-[(2,2,5,7,8-pentamethyl-3,4-dihydrochromen-6-yl)sulfonylamino]methylidene]amino]-2-(phenylmethoxycarbonylamino)pentanoic acid
• CAS: 112160-32-4
• 化学式: C₂₈H₃₈N₄O₇S
• 分子量: 574.698
• InChiKey: FOBDSZYESKTHJZ-QFIPXVFZSA-N

物化性质

• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  178
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Z-Arg(Pmc)-OH 在 钯 氢气 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 4.0h， 生成 Boc-L-Cys(Acm)-L-Arg(Pmc)-OH
  参考文献：
  名称：

  Peptide synthesis by prior thiol capture. 6. Rates of the disulfide-bond-forming capture reaction and demonstration of the overall strategy by synthesis of the C-terminal 29-peptide sequence of BPTI

  摘要：

  DOI：

  10.1021/jo00273a008
• 作为产物：
  描述：

  2,3,5-三甲基苯酚 在 氯磺酸 、 sodium hydroxide 、 zinc(II) chloride 作用下， 以 氯仿 、 溶剂黄146 、 丙酮 为溶剂， 反应 24.25h， 生成 Z-Arg(Pmc)-OH
  参考文献：
  名称：

  用于肽合成的酸不稳定的精氨酸衍生物：N G -2,2,2,5,7,8-五甲基苯并吡喃-6-磺酰基-L-精氨酸

  摘要：

  已经开发出用于精氨酸的胍侧链功能的三氟乙酸（TFA）不稳定的保护基。Ñ ģ - （2,2,5,7,8-五甲基-6-磺酰基-L-精氨酸在室温下迅速裂解以TFA或50％TFA的二氯甲烷溶液Fmoc.Arg（PMC）·OH的制剂和描述了Bnpeoc.Arg（Pmc）.OH。

  DOI：

  10.1016/s0040-4020(01)86564-9

文献信息

• Targeting integrins: Insights into structure and activity of cyclic RGD pentapeptide mimics containing azabicycloalkane amino acids
  作者：Laura Belvisi、Anna Bernardi、Matteo Colombo、Leonardo Manzoni、Donatella Potenza、Carlo Scolastico、Giuseppe Giannini、Marcella Marcellini、Teresa Riccioni、Massimo Castorina、Pietro LoGiudice、Claudio Pisano

  DOI：10.1016/j.bmc.2005.08.048

  日期：2006.1

  integrin antagonist. Structure determination of the cyclic RGD pentapeptide mimics performed by a combination of NMR spectroscopy, and molecular mechanics and dynamics calculations showed a strong dependence of the RGD cyclopeptide conformation on lactam ring size and stereochemistry. ST1646 revealed the highest ability within the library to adopt the proper RGD orientation required for binding to the alpha(v)beta3

  合成了包含立体异构体5,6-和5,7-稠合的双环内酰胺的环状RGD五肽模拟物的小文库。发现该文库包含α（v）beta3整联蛋白的高亲和力配体。这项研究的目的是调查这些配体的活性，选择性和结构，以鉴定可以被评估为肿瘤血管生成抑制剂的新的特异性α（v）-整联蛋白拮抗剂。体外筛选，包括对纯化的alpha（v）beta3，alpha（v）beta5和alpha5beta1整联蛋白的受体结合测定，以及血小板聚集测定，表明ST1646是一种有效的，高度选择性的alpha（v）beta3 / alpha（v） beta5整合素拮抗剂。环状RGD五肽模拟物的结构测定是通过NMR光谱结合进行的，分子力学和动力学计算表明，RGD环肽构象对内酰胺环的大小和立体化学有很强的依赖性。ST1646揭示了文库中具有最高能力来采取与α（v）beta3整联蛋白结合所需的正确RGD方向，这是由最近解析的整齐蛋白α（v）bet
• Oligopeptides derived from C-reactive protein fragments
  申请人：Italfarmaco S.p.A.

  公开号：US06057295A1

  公开（公告）日：2000-05-02

  Oligopeptides derived from fragments of C-reactive proteins and their use as immunomodulating agents in the therapy of cardiovascular and inflammatory diseases.

  C-反应蛋白片段衍生的寡肽及其在心血管和炎症性疾病治疗中作为免疫调节剂的应用。
• Design and evaluation of Trypanosoma brucei metacaspase inhibitors
  作者：Maya Berg、Pieter Van der Veken、Jurgen Joossens、Venkatraj Muthusamy、Matthias Breugelmans、Catherine X. Moss、Jana Rudolf、Paul Cos、Graham H. Coombs、Louis Maes、Achiel Haemers、Jeremy C. Mottram、Koen Augustyns

  DOI：10.1016/j.bmcl.2010.01.099

  日期：2010.3

  Metacaspase (MCA) is an important enzyme in Trypanosoma brucei, absent from humans and differing significantly from the orthologous human caspases. Therefore MCA constitutes a new attractive drug target for antiparasitic chemotherapeutics, which needs further characterization to support the discovery of innovative drug candidates. A first series of inhibitors has been prepared on the basis of known substrate specificity and the predicted catalytic mechanism of the enzyme. In this Letter we present the first inhibitors of TbMCA2 with low micromolar enzymatic and antiparasitic activity in vitro combined with low cytotoxicity. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthetic Multifunctional Pores with External and Internal Active Sites for Ligand Gating and Noncompetitive Blockage
  作者：Virginie Gorteau、Florent Perret、Guillaume Bollot、Jiri Mareda、Adina N. Lazar、Anthony W. Coleman、Duy-Hien Tran、Naomi Sakai、Stefan Matile

  DOI：10.1021/ja045987+

  日期：2004.10.1

  Design, synthesis, and multifunctionality of p-octiphenyl beta-barrel pores with external LRL triads and internal HH dyads are described. Molecular recognition of anionic fullerenes > calixarenes > pyrenes by guanidinium arrays at the outer pore surface is shown to result in pore opening, whereas alpha-helix recognition within the topologically matching internal space is shown to result in noncompetitive pore blockage. This experimental evidence for multifunctionality is supported by comparison with pertinent control pores and blockers, by structural studies using FRET from p-octiphenyl donors in the pore to BODIPY acceptors in the bilayer, and by molecular mechanics simulations. Practical usefulness of ligand-gated synthetic multifunctional pores is exemplified with the continuous detection of chemical processes.
• Outer surface modification of synthetic multifunctional pores
  作者：Pinaki Talukdar、Naomi Sakai、Nathalie Sordé、David Gerard、Valérie M.F. Cardona、Stefan Matile

  DOI：10.1016/j.bmc.2003.06.002

  日期：2004.3

  The characteristics of pores formed by p-octiphenyl beta-barrels with LWV triads at the outer surface are reported in comparison with the conventional rigid-rod P-barrels with all-L outer surface. Maintained multifunctionality of tetrameric pores with external LWV triads (inversion of ion selectivity, molecular recognition and transformation) is implicative for intact barrel interior. Increased pore activity supports dominance of high bilayer affinity for W over low affinity for V. Transmembrane p-octiphenyl orientation (from fluorescence depth quenching) supports barrel-stave (rather than toroidal) pores and dominance of transmembrane preference of rigid rods over interfacial preference of W. Destabilization of beta-barrel pores in membranes (from short single-channel lifetimes) and in the media (from 4th-power dependence on monomer concentration) by LWV triads supports dominance of low P-propensity for W over high P-propensity for V. The relation between the stability of supramolecular (pre)pores and dependence of activity on monomer concentration is discussed in a more general context. (C) 2003 Elsevier Ltd. All rights reserved.